Ok my guess (Lets see I will get 2 things right, thanks chateau) of what happens for this episode.
All teams arrive in Florence and travel to the first route marker were they hit an hours of Operation.
The next morning (the 21st) teams rush to the clue box and find both a clue box and a pull a number (or write your team down ect).
The first two to this are Jennifer and Nathan and Tk & Rachel, followed by the Goths, Ron & Christina and Nicolas and Donald.
Clue: Roadblock (which we know) and the Fast Forward Clue.
I do believe there is a limit of either staggered departure times for teams in the air (thus no following another) or only two teams at a time in the air).
I believe that Nic & Don must be last or near last for sign up and thus why they choose to go for the Fast Forward. I also believe that Nate & Jenn are probably first as to why the team has been wanting a win so bad, don't go for the Fast Forward.
I am beginning to think that the Goths don't go for the Fast Forward (but I am really unsure).
Teams then go to the detour. Where I assume that Jennifer and Nathan do fine and actually finish first. I then think Rachel & Tk do it (the detour, not IT) but they choose the other option as coordination doesn't seem to be something they are good at.
I think the Goths are the ones to loose their clue and get lost (we know they get lost to some degree) and this is what puts them hours behind, and I think we see them arguing over guesses over where they are going.
I think Ron & Christina get to the detour and are the team that falls apart doing the detour (this could be due to his hernia and its build up). And that could certainly put them an hour plus behind.
Plus I don't think The Goths would have problems with this task (though it is possible that it is Tk & Rachel).
I think Don after being a pussy for a few minutes man's up and gets the tattoo, and that either team grandpa or Natan and Jennifer are team #1.
That Tk & rachel are team number 3.
That Ronald & Christina are team number 4, and that he has the quote. And this is one of the reasons I think that the Goths didn't go for the Fast Forward, because if two teams are known to go for the Fast Forward then the other teams know that they have what should be a large cushion of time for any errors they make.
But I am probably wrong.